Copper/GanPhos-Catalyzed 1,3-Dipolar Cycloaddition of Azo­methine Ylides: An Efficient Access to Chiral Pyrrolidine Spirocycles

Abstract

A highly efficient copper/GanPhos-catalyzed 1,3-dipolar cyclo­addition­ of azomethine ylides is reported. This viable transformation provides a series of optically active spiro[dihydronaphthalene-2,3′-pyrrolidine]s, bearing one spiro quaternary and three tertiary stereogenic centers, in good yields and with high ee values. This protocol features high diastereo- and enantioselectivity, broad substrate scope and mild reaction conditions.

Key words

pyrrolidine spirocycles - 1,3-dipolar cycloaddition - azo­methine ylides - stereogenic centers - copper - GanPhos

Publikationsverlauf

Eingereicht: 01. Juli 2020

Angenommen nach Revision: 20. Oktober 2020

Artikel online veröffentlicht:
17. November 2020

• References


For selected examples, see:
• 1a Galliford CV, Scheidt KA. Angew. Chem. Int. Ed. 2007; 46: 8748
• 1b Harvey AL. Drug Discovery Today 2008; 13: 894
• 1c Li JW. H, Vederas JC. Science 2009; 325: 161
• 2a Obniska J, Byrtus H, Kamiński K, Pawłowski M, Szczesio M, Karolak-Wojciechowska J. Bioorg. Med. Chem. 2010; 18: 6134
• 2b Obniska J, Kołaczkowski M, Bojarski A, Duszyńska B. Eur. J. Med. Chem. 2006; 41: 874
• 3 Jiang B, Xu M. Angew. Chem. Int. Ed. 2004; 43: 2543
• 4 Tomita M, Okamoto Y, Kikuchi T, Osaki K, Nishikawa M, Kamiya K, Sasaki Y, Matoba K, Goto K. Chem. Pharm. Bull. 1971; 19: 770

For selected examples, see:
• 5a Wei L, Chang X, Wang C.-J. Acc. Chem. Res. 2020; 53: 1084
• 5b Maroto EE, Izquierdo M, Reboredo S, Marco-Martínez J, Filippone S, Martín N. Acc. Chem. Res. 2014; 47: 2660
• 5c Hashimoto T, Maruoka K. Chem. Rev. 2015; 115: 5366
• 5d Bdiri B, Zhao B.-J, Zhou Z.-M. Tetrahedron: Asymmetry 2017; 28: 876
• 5e Adrio J, Carretero JC. Chem. Commun. 2014; 50: 12434
• 5f Fang X, Wang C.-J. Org. Biomol. Chem. 2018; 16: 2591
• 5g Adrio J, Carretero JC. Chem. Commun. 2019; 55: 11979
• 5h Han R, Ding Y, Jin X, Li E.-Q. Org. Biomol. Chem. 2020; 18: 646
• 5i Cui H, Li K, Wang Y, Song M, Wang C, Wei D, Li E.-Q, Duan Z, Mathey F. Org. Biomol. Chem. 2020; 18: 3740
• 5j Liu T.-L, Xue Z.-Y, Tao H.-Y, Wang C.-J. Org. Biomol. Chem. 2011; 9: 1980
• 5k Liu T.-L, He Z.-L, Li Q.-H, Tao H.-Y, Wang C.-J. Adv. Synth. Catal. 2011; 353: 1713
• 5l Li Q.-H, Liu T.-L, Wei L, Tao H.-Y, Wang C.-J. Chem. Commun. 2013; 49: 9642
• 5m Meng X, Du Y, Zhang Q, Yu A, Zhang Y, Jia J, Liu X. Asian J. Org. Chem. 2017; 6: 1719
• 6 Allway P, Grigg R. Tetrahedron Lett. 1991; 32: 5817
• 7 Liu Y, Li W, Zhang J. Natl. Sci. Rev. 2017; 4: 326

For selected examples, see:
• 8a Antonchick AP, Gerding-Reimers C, Catarinella M, Schürmann M, Preut H, Ziegler S, Rauh D, Waldmann H. Nat. Chem. 2010; 2: 735
• 8b Takayama H, Jia Z.-J, Kremer L, Bauer JO, Strohmann C, Ziegler S, Antonchick AP, Waldmann H. Angew. Chem. Int. Ed. 2013; 52: 12404

For selected examples, see:
• 9a Liu T.-L, He Z.-L, Wang C.-J. Chem. Commun. 2011; 47: 9600
• 9b Teng H.-L, Huang H, Wang C.-J. Chem. Eur. J. 2012; 18: 12614
• 9c Liu H.-C, Liu K, Xue Z.-Y, He Z.-L, Wang C.-J. Org. Lett. 2015; 17: 5440
• 9d Liu H.-C, Tao H.-Y, Cong H, Wang C.-J. J. Org. Chem. 2016; 81: 3752
• 9e Shen C, Yang Y, Wei L, Dong W.-W, Chung LW, Wang C.-J. iScience 2019; 11: 146

For selected examples, see:
• 10a Zhang Z.-M, Xu B, Xu S, Wu H.-H, Zhang J. Angew. Chem. Int. Ed. 2016; 55: 6324
• 10b Xu B, Zhang Z.-M, Xu S, Liu B, Xiao Y, Zhang J. ACS Catal. 2017; 7: 210
• 10c Liu B, Zhang Z.-M, Xu B, Xu S, Wu H.-H, Zhang J. Adv. Synth. Catal. 2018; 360: 2144
• 10d Wang L, Chen M, Zhang J. Org. Chem. Front. 2019; 6: 694

For selected examples, see:
• 11a Liu Y.-Z, Shang S.-J, Yang W.-L, Luo X, Deng W.-P. J. Org. Chem. 2017; 82: 11141
• 11b Liu Y.-Z, Shang S.-J, Zhu J.-Y, Yang W.-L, Deng W.-P. Adv. Synth. Catal. 2018; 360: 2191
• 11c Deng H, Jia R, Yang W.-L, Yu X, Deng W.-P. Chem. Commun. 2019; 55: 7346
• 11d Zou X.-J, Yang W.-L, Zhu J.-Y, Deng W.-P. Chin. J. Chem. 2020; 38: 435

For other ligands used for 1,3-dipolar cycloadditions of azomethine ylides, see:
• 12a Awata A, Arai T. Chem. Eur. J. 2012; 18: 8278
• 12b Arai T, Ogawa H, Awata A, Sato M, Watabe M, Yamanaka M. Angew. Chem. Int. Ed. 2015; 54: 1595
• 12c Deng H, He F.-S, Li C.-S, Yang W.-L, Deng W.-P. Org. Chem. Front. 2017; 4: 2343
• 12d Zhu J.-Y, Yang W.-L, Liu Y.-Z, Shang S.-J, Deng W.-P. Org. Chem. Front. 2018; 5: 70
• 12e Xu S, Zhang Z.-M, Xu B, Liu B, Liu Y, Zhang J. J. Am. Chem. Soc. 2018; 140: 2272
• 12f Cheng F, Kalita SJ, Zhao Z.-N, Yang X, Zhao Y, Schneider U, Shibata N, Huang Y.-Y. Angew. Chem. Int. Ed. 2019; 58: 16637
• 13a Zhi M, Gan Z, Ma R, Cui H, Li E.-Q, Duan Z, Mathey F. Org. Lett. 2019; 21: 3210
• 13b Gan Z, Zhi M, Han R, Li E.-Q, Duan Z, Mathey F. Org. Lett. 2019; 21: 2782
• 14a Xi Q.-Z, Gan Z.-J, Li E.-Q, Duan Z. Eur. J. Org. Chem. 2018; 4917
• 14b Li E, Jin H, Huang Y. ChemistrySelect 2018; 3: 12007
• 14c Gan Z, Gong Y, Chu Y, Li E.-Q, Huang Y, Duan Z. Chem. Commun. 2019; 55: 10120
• 14d Ma R, Song G, Xi Q, Yang L, Li E.-Q, Duan Z. Chin. J. Org. Chem. 2019; 39: 2196
• 14e Li E.-Q, Huang Y. Chem. Commun. 2020; 56: 680
• 15 CCDC 1969641 (3oa) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
• 16a Teng H.-L, Yao L, Wang C.-J. J. Am. Chem. Soc. 2014; 136: 4075
• 16b Xue Z.-Y, Liu T.-L, Lu Z, Huang H, Tao H.-Y, Wang C.-J. Chem. Commun. 2010; 46: 1727
• 16c Imae K, Konno T, Ogata K, Fukuzawa S. Org. Lett. 2012; 14: 4410
• 16d Gong Y.-C, Wang Y, Li E.-Q, Cui H, Duan Z. Adv. Synth. Catal. 2019; 361: 1389
• 17a Rahman AF. M. M, Ali R, Jahng Y, Kadi AA. Molecules 2012; 17: 571
• 17b Zubia A, Mendoza L, Vivanco S, Aldaba E, Carrascal T, Lecea B, Arrieta A, Zimmerman T, Vidal-Vanaclocha F, Cossío FP. Angew. Chem. Int. Ed. 2005; 44: 2903